Personal Care Compositions with Silicones And

(19) &

(11) EP 1 804 922 B1

(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61Q 19/00 (2006.01) A61Q 1/02 (2006.01) 13.02.2008 Bulletin 2008/07 A61Q 19/10 (2006.01) A61Q 5/02 (2006.01) A61Q 5/12 (2006.01) A61Q 15/00 (2006.01) (2006.01) (2006.01) (21) Application number: 05797352.1 A61Q 11/00 A61K 8/896 A61K 8/891 (2006.01) A61K 8/58 (2006.01) A61K 8/898 (2006.01) A61K 8/41 (2006.01) (22) Date of filing: 24.10.2005 (86) International application number: PCT/EP2005/011416

(87) International publication number: WO 2006/045583 (04.05.2006 Gazette 2006/18)

(54) PERSONAL CARE COMPOSITIONS WITH SILICONES AND DIHYDROXYPROPYL TRIALKYL AMMONIUM SALTS KÖRPERPFLEGEZUSAMMENSETZUNGEN MIT SILIKONEN UND DIHYDROXYPROPYL- TRIALKYL-AMMONIUMSALZEN COMPOSITIONS DE SOINS PERSONNELS COMPRENANT DES COMPOSES SILICONES ET DES SELS DE DIHYDROXYPROPYL TRIALKYL AMMONIUM

(84) Designated Contracting States: • MINER, Philip E. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Unilever Home&Personal Care USA HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI Trumbull, CT 06611 (US) SK TR • BARROW, Stephen Unilever Home&Personal Care USA (30) Priority: 25.10.2004 US 972483 Trumbull, CT 06611 (US) 08.09.2005 US 222189 • CHANDAR, Prem Unilever Home&Personal Care USA (43) Date of publication of application: Trumbull, CT 06611 (US) 11.07.2007 Bulletin 2007/28 • MCMANUS, Richard Unilever Home&Personal Care USA (73) Proprietors: Trumbull, CT 06611 (US) • UNILEVER PLC • HARICHIAN, Bijan London, Greater London EC4P 4BQ (GB) Unilever T. V. A. Company LLC Designated Contracting States: SantaBarbara, CA 93101 (US) CY GB IE • UNILEVER N.V. (74) Representative: Acham, Nicholas Clive 3013 AL Rotterdam (NL) Unilever Patent Group Designated Contracting States: Colworth House AT BE BG CH CZ DE DK EE ES FI FR GR HU IS IT Sharnbrook LI LT LU LV MC NL PL PT RO SE SI SK TR Bedford, MK44 1LQ (GB)

(72) Inventors: (56) References cited: • HURLEY, Megan K. EP-A- 0 930 066 WO-A-90/03161 Unilever Home&Personal Care USA WO-A-96/35410 WO-A-97/07779 Trumbull, CT 06611 (US) US-B1- 6 869 977

Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 804 922 B1

Printed by Jouve, 75001 PARIS (FR) EP 1 804 922 B1

Description

Field of the Invention

5 [0001] The invention concerns personal care compositions formulated to impart moisturization and having excellent skinfeel properties.

The Related Art

10 [0002] Dry skin is a problem in varying degree to most humans. This condition is particularly evident in winter. Personal care products such as skin creams/lotions, shampoos/ conditioners, toilet bars/shower gels and antiperspirants/deodorants are normally formulated with at least one material to address dry skin. Symptoms such as itching, flaking and a visually displeasing dermal appearance can all to some extent be modulated. [0003] There are three traditional classes of materials employed against the problem. Occlusives such as petrolatum 15 or silicone oils serve to inhibit loss of natural moisture. They form a barrier between the epidermis and the environment. Another approach is the use of keratolytic agents to enhance rate of dermal exfoliation. Alpha-hydroxy acids are the most common agents for achieving exfoliation. [0004] A third approach to dry skin is topical application of humectants. Hydroxylated monomeric and polymeric organic substances are generally used for this purpose. Glycerin known also as glycerol is one of the most effective humectants. 20 [0005] Quaternary ammonium compounds have recently been commercialized as moisturizers. One of these known under the trademark Honeyquat 50 with INCI name of Hydroxypropyltrimonium Honey has been reported to be a better humectant than glycerin at levels of 2%. See the Arch/Brooks brochure titled "Cosmetic Ingredients & Ideas®", Issue No. 2, August 2001. Honeyquat 50 is described as being derived from the reaction of pendent hydroxyl groups (on the disaccharide) of a "light" deodorized grade of honey with a chlorohydroxytrimethylammonium derivative. Another com- 25 mercial quaternary ammonium moisturizer is Cola™Moist 200 with INCl name of Hydroxypropyl Bis-Hydroxyethyldimo- nium Chloride. See the Colonial Chemical Inc. brochure titled "Cola™Moist 200", copyright 2004. U.S. Patent 6,869,977 B1 (O’Lenick, Jr. et al.) to Colonial Chemical Inc. discloses a related monocationic material described as a moisturizing agent. [0006] Many moisturizing actives impart to their formulas an aesthetically displeasing tack and/or sticky skinfeel. The 30 present invention sought to provide a silicone containing moisturizing personal care composition having consumer pleasing skinfeel properties.

SUMMARY OF THE INVENTION

35 [0007] A personal care composition is provided which includes:

(i) from 0.05% to 30% by weight of a dihydroxypropyl quaternary ammonium salt of structure AB,

wherein A is a cationic charged component of the salt AB, 40 B is an anionic charged component of the salt AB, and A has a single quaternized nitrogen atom, at least two hydroxy groups and a molecular weight no higher than 250;

(ii) from 0.05 to about 50% by weight of a silicone.

45 DETAILED DESCRIPTION OF THE INVENTION

[0008] Now it has been found that the skinfeel properties of moisturizing silicone compositions can be improved through inclusion of dihydroxypropyl quaternary ammonium salts as detackifying agents. [0009] Thus, an important material of the present invention is dihydroxypropyl quaternary ammonium salts of structure 50 AB, wherein A is a cationic charged component of the salt AB, and B is an anionic charged component of the salt AB, A has one quaternized nitrogen atom, at least two hydroxyl groups and a molecular weight no higher than 50 but preferably no higher than 200, and optimally no higher than 170. [0010] Anionic charged component B may be organic or inorganic with proviso that the material is cosmetically acceptable. Typical inorganic anions are halides, sulfates, phosphates, nitrates and borates. Most preferred are the halides, 55 especially chloride. Organic anionic counter ions include methosulfate, toluoyl sulfate, acetate, citrate, tartrate, lactate, gluconate, and benzenesulfonate. The number and charge of negatively charged component B will be sufficient to neutralize the positive charge of component A. [0011] A preferred embodiment of the quaternary ammonium salts is the dihydroxypropyl tri (C1-C3 alkyl or hydroxyalkyl)

2 EP 1 804 922 B1

ammonium salts. [0012] These salts may be obtained in a variety of synthetic procedures, most particularly by hydrolysis of chlorohy- droxyprppyltri(C1-C3 alkyl or hydroxyalkyl) ammonium salts. Ordinarily the C1-C3 alkyl or hydroxyalkyl constituent on the quaternized ammonium group will be methyl, ethyl, n-propyl, isopropyl, hydroxyethyl, hydroxymethyl and mixtures 5 thereof. Particularly preferred is a trimethyl ammonium group known through INCl nomenclature as a "trimonium" group. A most preferred species is 1,2-dihydroxypropyltrimonium chloride, wherein the C1-C3 alkyl is a methyl group. [0013] Another useful species of the quaternary ammonium salts is the material of structure (I).

20 [0014] Amounts of the quaternary ammonium salts may range from 0.05 to 30%, preferably from 0.1 to 25%, more preferably from 5 to 20%, optimally from 10 to 15% by weight of the composition. [0015] The moisturizing compositions of this invention will include a silicone. A wide variety of silicones including materials of liquid, solid or semi-solid consistency at room temperature can be useful for this invention. Liquid silicones 25 include silicone oils which may be divided into the volatile and nonvolatile variety. The term "volatile" as used herein refers to those materials which have a measurable vapor pressure at ambient temperature. Volatile silicone oils are preferably chosen from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing from 3 to 9, preferably from 4 to 5, silicon atoms. Commercially available volatile silicone oils include DC 200, DC 244, DC 245, DC 344 and DC 345, all supplied by the Dow Corning Corporation; SF-1204, SF-1202 Silicone Fluids, GE 7207 and GE 7158 sourced 30 from GE Silicones; and SWS-03314 sourced from SWS Silicones Corporation. [0016] Useful nonvolatile silicone oils include polyalkyl siloxanes, polyalkylaryl siloxanes and polyether siloxane copolymers. The essentially nonvolatile polyalkyl siloxanes useful herein include, for example, polydimethyl siloxanes with viscosities of from 5 x 10-16 to 0.1 m2/s at 25°C. Among the preferred nonvolatile emollients useful in the present compositions are the polydimethyl siloxanes having viscosities from 1 x 10-5 to 4 x 10-4 m2/s at 25°C. Representative 35 commercial materials include polyalkyl siloxanes sold under the Viscasil Series from G.E. Silicones, and the DC 200 series sold by the Dow Corning Corporation. Polyalkylaryl siloxanes including polymethylphenyl siloxanes such as SF 1075 methyl-phenyl fluid and 556 Cosmetic Grade Fluid (sold by Dow Corning Corporation) may also be useful. Illustrative polyoxyalkylene ether copolymers are commercially available as SF 1066 from G.E. Silicones, and PEG-10 Dimethicone available from Shin-Etsu. 40 [0017] Another class of nonvolatile silicones are emulsifying and non- emulsifying silicone elastomers. Representative of this category is Dimethicone/Vinyl Dimethicone Crosspolymer available as Dow Corning 9040, General Electric SFE 839, and Shin-Etsu KSG-18. Silicone waxes such as Silwax WS-L (Dimethicone Copolyol Laurate) may also be useful. [0018] Amounts of the silicone may range from 0.05 to 50%, preferably from 0.5 to 40%, more preferably from 2 to 20%, optimally from 5 to 12% by weight of the composition. 45 [0019] Emollient materials may serve as cosmetically acceptable carriers. These may be in the form of natural or synthetic esters and hydrocarbons. Amounts of the emollients may range anywhere from 0.1 to 60%, preferably between 1 and 30% by weight of the composition. [0020] Among the ester emollients are:

50 (a) Alkyl esters of saturated fatty acids having 10 to 24 carbon atoms. Examples thereof include behenyl neopen- tanoate, isononyl isonanonoate, isopropyl myristate and octyl stearate.

(b) Ether-esters such as fatty acid esters of ethoxylated saturated fatty alcohols.

55 (c) Polyhydric alcohol esters. Ethylene glycol mono and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol (200-6000) mono- and di-fatty acid esters, propylene glycol mono- and di- fatty acid esters, polypropylene glycol 2000 monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, polyglycerol poly-fatty esters, ethoxylated glyceryl mono-stearate, 1,3-butylene glycol monos-

3 EP 1 804 922 B1

tearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid ester, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters. Particularly useful are pentaerythritol, trimethylolpropane and neopentyl glycol esters of C1-C30 alcohols.

5 (d) Wax esters such as beeswax, spermaceti wax and tribehenin wax.

(e) Sugar ester of fatty acids such as sucrose polybehenate and sucrose polycottonseedate.

[0021] Natural ester emollients principally are based upon mono-, di- and tri- glycerides. Representative glycerides 10 include sunflower seed oil, cottonseed oil, borage oil, borage seed oil, primrose oil, castor and hydrogenated castor oils, rice bran oil, soybean oil, olive oil, safflower oil, shea butter, jojoba oil and combinations thereof. Animal derived emollien ts are represented by lanolin oil and lanolin derivatives. Amounts of the natural esters may range from 0.1 to 20% by weight of the compositions. [0022] Hydrocarbons which are suitable cosmetically acceptable carriers include petrolatum, mineral oil,11 C-C13 15 isoparaffins, polybutenes, and especially isohexadecane, available commercially as Permethyl 101A from Presperse Inc. [0023] Fatty acids having from 10 to 30 carbon atoms may also be suitable as cosmetically acceptable carriers. Illustrative of this category are pelargonic, lauric, myristic, palmitic, stearic, isostearic, oleic, linoleic, linolenic, hydroxy- stearic and behenic acids. [0024] Surfactants may also be present in compositions of the present invention. Total concentration of the surfactant 20 when present may range from 0.1 to 50%, preferably from 1 to 25%, optimally from 1 to 10% by weight of the composition, and being highly dependent upon the type of personal care product. The surfactant may be selected from the group consisting of anionic, nonionic, cationic and amphoteric actives. Particularly preferred nonionic surfactants are those with a C10-C20 fatty alcohol or acid hydrophobe condensed with from 2 to 100 moles of ethylene oxide or propylene oxide per mole of hydrophobe; C2-C10 alkyl phenols condensed with from 2 to 20 moles of alkylene oxide; mono- and 25 di-fatty acid esters of ethylene glycol; fatty acid monoglyceride; sorbitan, mono- and di- C8-C20 fatty acids; and polyoxyethylene sorbitan as well as combinations thereof. Alkyl polyglycosides and saccharide fatty amides (e.g. methyl glu- conamides) and trialkylamine oxides are also suitable nonionic surfactants. [0025] Preferred anionic surfactants include soap, alkyl ether sulfates and sulfonates, alkyl sulfates and sulfonates, alkylbenzene sulfonates, alkyl and dialkyl sulfosuccinates, CB-C20 acyl isethionates, C8-C20 alkyl ether phosphates, 30 C8-C20 sarcosinates, C8-C20 acyl factylates, sulfoacetates and combinations thereof. [0026] Useful amphoteric surfactants include cocoamidopropyl betaine, C12-C20 trialkyl betaines, sodium lauroamphoacetate, and sodium laurodiamphoacetate. [0027] Adjunct humectants may be employed in the present invention. These are generally polyhydric alcohol-type materials. Typical polyhydric alcohols include glycerin, propylene glycol, dipropylene glycol, polypropylene glycol, pol- 35 yethylene glycol, sorbitol, hydroxypropyl sorbitol, hexylene glycol, 1; 3-butylene glycol, isoprene glycol, 1,2,6-hexanetriol, ethoxylated glycerol, propoxylated glycerol and mixtures thereof. The amount of adjunct humectant may range anywhere from 0.2 to 40%, preferably between 1 and 25%, most preferably between 2 and 15% by weight of the composition. Most preferred is glycerin as an adjunct humectant or moisturizer. [0028] Sunscreen agents may also be included in compositions of the present invention. Particularly preferred are 40 such materials as ethylhexyl p- methoxycinnamate, available as Parsol MCX®, Avobenzene available as Parsol 1789®, and benzophenone-3 also known as Oxybenzone. Inorganic sunscreen actives may be employed such as microfine (1 to 100 nm) titanium dioxide and zinc oxide. Amounts of the sunscreen agents when present may generally range from 0.1 to 30%, preferably from 2 to 20%, optimally from 4 to 10% by weight of the composition. [0029] Antiperspirants and deodorant compositions of the present invention ordinarily will contain astringent actives. 45 Examples include aluminum chloride, aluminum chlorhydrex, aluminim- zirconium chlorhydrex glycine, aluminum sulfate, zinc sulfate, zirconium and aluminum chlorohydroglycinate, zirconium hydroxychloride, zirconium and aluminum lactate, zinc phenolsulfonate and combinations thereof. Amounts of the astringents may range anywhere from 0.5 to 50% by weight of the composition. [0030] Dental products formulated according to the present invention will generally contain a fluoride source to prevent 50 dental caries. Typical anti-caries actives include sodium fluoride, stannous fluoride and sodium monofluoro phosphate. Amounts of these materials will be determined by the amount of fluoride releasable which should range between about 500 to about 8800 ppm of the composition. Other components of dentifrices can include desensitizing agents such as potassium nitrate and strontium nitrate, sweeteners such as sodium saccharine, aspartame, sucralose, and potassium acesulfam. Thickeners, opacifying agents, abrasives and colorants will normally also be present. 55 [0031] Preservatives can desirably be incorporated into the personal care compositions of this invention to protect against the growth of potentially harmfulmicroorganisms. Particularly preferred preservatives are phenoxyethanol, methyl paraben, propyl paraben, imidazolidinyl urea, dimethyloldimethylhydantoin, ethylenediaminetetraacetic acid salts (ED- TA), sodium dehydroacetate, methylchloroisothiazolinone, methylisothiazolinone, iodopropynbutylcarbamate and benzyl

4 EP 1 804 922 B1

alcohol. The preservatives should be selected having regard for the use of the composition and possible incompatibilities between the preservatives and other ingredients. Preservatives are preferably employed in amounts ranging from 0.0001 % to 2% by weight of the composition. [0032] Compositions of the present invention may include vitamins. Illustrative vitamins are Vitamin A (retinol), Vitamin 5 B2, Vitamin B3 (niacinamide), Vitamin B6, Vitamin C, Vitamin E, Folic Acid and Biotin. Derivatives of the vitamins may also be employed. For instance, Vitamin C derivatives include ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate and ascorbyl glycoside. Derivatives of Vitamin E include tocopheryl acetate, tocopheryl palmitate and tocopheryl linoleate. DL-panthenol and derivatives may also be employed. Total amount of vitamins when present in compositions according to the present invention may range from 0.001 to 10%, preferably from 0.01 % to 1%, optimally from 0.1 to 0.5% by 10 weight of the composition. [0033] Another type of useful substance can be that of an enzyme such as amylases, oxidases, proteases, lipases, cellulases, elastases and combinations. [0034] Skin lightening compounds may be included in the compositions of the invention. Illustrative substances are placental extract, lactic acid, niacinamide, arbutin, kojic acid, ferulic acid, resorcinol and derivatives including 4- substituted 15 resorcinols and combinations thereof. Amounts of these agents may range from 0.1 to 0%, preferably from 0.5 to 2% by weight of the composition. [0035] Desquamation promoters may be present. Illustrative are the alpha- hydroxycarboxylic acids and beta- hydrox- ycarboxylic acids. The term "acid" is meant to include not only the free acid but also salts and C 1-C30 alkyl or aryl esters thereof and lactones generated from removal of water to +form cyclic or linear lactone structures. Representative acids 20 are glycolic, lactic and malic acids. Salicylic acid is representative of the beta-hydroxycarboxylic acids. Amounts of these materials when present may range from 0.01 to 15% by weight of the composition. [0036] A variety of herbal extracts may optionally be included in compositions of this invention. The extracts may either be water soluble or water-insoluble carried in a solvent which respectively is hydrophilic or hydrophobic. Water and ethanol are the preferred extract solvents. Illustrative extracts include those from green tea, chamomile, licorice, aloe 25 vera, grape seed, citrus unshui, willow bark, sage, thyme and rosemary. [0037] Also included may be such materials as lipoic acid, retinoxytrimethylsilane (available from Clariant Corp. under the Silcare 1 M-75 trademark), dehydroepiandrosterone (DHEA) and combinations thereof. Ceramides (including Ce- ramide 1, Ceramide 3, Ceramide 3B and Ceramide 6) as well as pseudoceramides may also be useful. Amounts of these materials may range from 0.000001 to 10%, preferably from 0.0001 to 1 % by weight of the composition. 30 [0038] Colorants, opacifiers and abrasives may also be included in compositions of the present invention. Each of these substances may range from 0.05 to 5%, preferably between 0.1 and 3% by weight of the composition. [0039] Personal care compositions of the present invention may be in any form. These forms may include lotions, creams, roll-on formulations, sticks, mousses, aerosol and non- aerosol sprays and fabric (e.g. nonwoven textile)-applied formulations. 35 [0040] A wide variety of packaging can be employed to store and deliver the personal care compositions. Packaging is often dependent upon the type of personal care end- use. For instance, leave-on skin lotions and creams, shampoos, hair conditioners and shower gels generally employ plastic containers with an opening at a dispensing end covered by a closure. Typical closures are screw-caps, non-aerosol pumps and flip-top hinged lids. Packaging for antiperspirants, deodorants and depilatories may involve a container with a roll-on ball on a dispensing end. Alternatively these types 40 of personal care products may be delivered as a stick composition formulation in a container with propel- repel mechanism where the stick moves on a platform towards a dispensing orifice. Metallic cans pressurized by a propellant and having a spray nozzle serve as packaging for antiperspirants, shave creams and other sprayable personal care products. Toilet bars may have packaging constituted by a cellulosic or plastic wrapper or within a cardboard box or even encompassed by a shrink wrap plastic film. 45 [0041] Another aspect of compositions of this invention may be the inclusion of instructions attached to or otherwise associated with the packaging. The instructions indicate to a consumer topical use of the composition on skin, hair or oral mucosae. Packaging itself will usually be printed with the instructions but sometimes a separate written insert within the package may serve to provide the instructions. Typical language includes phrases such as "apply a thin layer to the underarm", "apply regularly to hands", "apply to wet hair, lather and rinse":, "cleanse skin" and "pump a small amount 50 onto the palm of your hand". [0042] The term "comprising" is meant not to be limiting to any subsequently stated elements but rather to encompass non-specified elements of major or minor functional importance. In other words the listed steps, elements or options need not be exhaustive. Whenever the words "including" or "having" are used, these terms are meant to be equivalent to "comprising" as defined above. 55 [0043] Except in the operating and comparative examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material are optionally to be understood as modified by the word "about". [0044] The following examples will more fully illustrate the embodiments of this invention. All parts, percentages and proportions referred to herein and in the appended claims are by weight unless otherwise illustrated.

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EXAMPLE 1

[0045] A representative personal care composition of the present invention in the form of a cosmetic lotion is outlined under Table I. 5 TABLE I INGREDIENT WEIGHT % PHASE A 10 Water Balance Disodium EDTA 0.05 Methyl Paraben 0.15 Magnesium Aluminum Silicate 0.60 15 Triethanolamine 1.20 Dihydroxypropyltrimonium Chloride 5.00 PHASE B 20 Xanthan Gum 0.20 Natrosol® 250HHR (ethyl cellulose) 0.50 Butylene Glycol 3.00

25 Glycerin 10.00 PHASE C Sodium Stearoyl Lactylate 0.10 Glycerol Monostearate 1.50 30 Stearyl Alcohol 1.50 Isostearyl Palmitate 3.00 Silicone Fluid 1.00

35 Cholesterol 0.25 Sorbitan Stearate 1.00 Butylated Hydroxy Toluene 0.05 Vitamin E Acetate 0.01 40 PEG-100 Stearate 2.00 Stearic Acid 3.00 Propyl Paraben 0.10

45 Parsol MCX® 2.00 Caprylic/Capric Triglyceride 0.50 Hydroxycaprylic Acid 0.01 C12-15 Alkyl Octanoate 3.00 50 PHASE D Vitamin A Palmitate 0.10 Bisabolol 0.01

55 Vitamin A Acetate 0.01 Fragrance 0.03

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(continued) INGREDIENT WEIGHT % PHASE A 5 Retinol 50C 0.02 Conjugated Linoleic Acid 0.50

EXAMPLE 2 10 [0046] A water-in-oil topical liquid make- up foundation according to the present invention is described in Table II below.

TABLE II INGREDIENT WEIGHT % 15 PHASE A Cyclomethicone 9.25 Oleyl Oleate 2.00 20 Dimethicone Copolyol 20.00 PHASE B Talc 3.38

25 Pigment (Iron Oxides) 10.51 Spheron L-1500 (Silica) 0.50 PHASE C Synthetic Wax Durachem 0602 10.10 30 Arachidyl Behenate 0.30 PHASE D Cyclomethicone 1.00

35 Trihydroxystearin 0.30 PHASE E Laureth-70.50 Propyl Paraben 0.25 40 PHASE F Fragrance 0.05 PHASE G

45 Water balance Dihydroxypropyltrimonium Chloride 4.00 Methyl Paraben 0.12 Propylene Glycol 8.00 50 Niacinamide 4.00 Glycerin 12.00 Sodium Chloride 2.00

55 Sodium Dehydroacetate 0.30

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EXAMPLE 3

[0047] Illustrated herein is a skin cream incorporating a quat salt and silicone of the present invention.

5 TABLE III INGREDIENT WEIGHT % Glycerin 15.00 Niacinamide 5.00 10 Dihydroxypropyltrimonium Chloride 5.00 Permethyl 101A1 3.00 Sepigel 3052 2.50

15 Q2-14033 2.00 Linseed Oil 1.33 Arlatone 21214 1.00 Cetyl Alcohol CO-1695 0.72 20 SEFA Cottonate5 0.67 Tocopherol Acetate 0.50 Panthenol 0.50 25 Stearyl Alcohol 0.48 Titanium Dioxide 0.40 Disodium EDTA 0.10 Glydant Plus6 0.10 30 PEG-100 Stearate 0.10 Stearic Acid 0.10 Purified Water Balance 35 1 Isohexadecane, Presperse Inc., South Plainfield, NJ 2 Potyacrylamide(and)C13-14 Isoparaffin(and) Laureth-7, Seppic Corporation, Fairfield, NJ 3 dimethicone(and)dimethiconol, Dow Corning 40 Corp. Midland, MI 4 Sorbitan Monostearate and Sucrococoate, ICI Americas Inc., Wilmington, DE 5 Sucrose ester of fatty acid 6 DMDM Hydantoin (and) lodopropynyl 45 Butylcarbamate, Lonza Inc., Fairlawn, NJ

EXAMPLE 4

50 [0048] Illustrative of another cosmetic composition incorporating the quat salt and a silicone according to the present invention is the formula of Table IV.

TABLE IV INGREDIENT WEIGHT % 55 Polysilicone-11 29 Cyclomethicone 59

8 EP 1 804 922 B1

(continued) INGREDIENT WEIGHT % Glycerin 10 5 Dihydroxypropyltrimonium Chloride 1.2 Dimethicone Copolyol 0.5 Sunflowerseed Oil 0.3

10 EXAMPLE 5

[0049] A relatively anhydrous composition incorporating the quat salt and a silicone of the present invention is reported in Table V.

15 TABLE V INGREDIENT WEIGHT % Cyclomethicone 60.65

20 Glycerin 15.00 Dimethicone 10.10 Squalane 6.00 Dihydroxypropyltrimonium Chloride 5.00 25 Isostearic Acid 1.90 Borage Seed Oil 0.90 Retinyl Palmitate 0.25

30 Ceramide 6 0.10 Tocopherol 0.10

EXAMPLE 6 35 [0050] An aerosol packaged foaming cleanser with a quat salt and silicone suitable for the present invention is outlined in Table VI.

TABLE VI 40 INGREDIENT WEIGHT % Sunflower Seed Oil 10.00 Glycerin 10.00

45 Maleated Soybean Oil 5.00 Silicone Urethane 1.00 Polyglycero-4 Oleate 1.00 Sodium C14-16 Olefin Sulfonate 15.00 50 Sodium Lauryl Ether Sulphate (25% active) 15.00 Cocoamidopropylbetaine 15.00 DC 1784® (Silicone Emulsion 50%) 5.00

55 Polyquatemium-11 1.00 Dihydroxypropyltrimonium Chloride 1.00 Water Balance

9 EP 1 804 922 B1

EXAMPLE 7

[0051] A disposable, single use personal care towelette product is described according to the present invention. A 70/30 polyester/rayon non-woven towelette is prepared with a weight of 1.8 grams and dimensions of 15 cm by 20 cm. 5 Onto this towelette is impregnated 1.0 grams of a composition including a quaternary ammonium salt and a silicone microemulsion as outlined in Table VII below.

TABLE VII INGREDIENT WEIGHT % 10 Dihydroxypropyltrimonium Chloride 4.00 Glycerin 12.00 Hexylene Glycol 2:00 15 Disodium Capryl Amphodiacetate 1.00 Gluconolactone 0.90 Silicone Microemulsion 0.85 Witch Hazel 0.50 20 PEG-40 Hydrogenated Castor Oil 0.50 Fragrance 0.20 Vitamin E Acetate 0.001 25 Water Balance

EXAMPLE 8

30 [0052] A toilet bar illustrative of the present invention is outlined under Table VIII.

TABLE VIII INGREDIENT WEIGHT % Sodium Soap (85/15 Tallow/ Coconut) 77.77 35 Dihydroxypropyltrimonium Chloride 3.50 Dimethicone 2.00 Sodium Chloride 0.77 40 Titanium Dioxide 0.40 Fragrance 1.50 Disodium EDTA 0.02

45 Sodium Etidronate 0.02 Fluorescer 0.024 Water Balance

50 EXAMPLE 9

[0053] A shampoo composition useful in the context of the present invention is described in Table IX below.

TABLE IX 55 Ingredient Weight % Ammonium Laureth Sulfate 12.00

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(continued) Ingredient Weight % Ammonium Lauryl Sulfate 2.00 5 Cocoamidopropyl Betaine 2.00 Sodium Lauroamphoacetate 2.00 Glycerin 12.00

10 Dihydroxypropyltrimonium Chloride 5.50 Ethylene Glycol Distearate 1.50 Cocomonoethanolamide 0.80 Cetyl Alcohol 0.60 15 Polyquaternium-10 0.50 Dimethicone 1.00 Zinc Pyridinethione 1.00

20 Sodium Citrate 0.40 Citric Acid 0.39 Sodium Xylene Sulfonate 1.00 Fragrance 0.40 25 Sodium Benzoate 0.25 Kathon CG® 0.0008 Benzyl Alcohol 0.0225

30 Water Balance

EXAMPLE 10

[0054] This Example illustrates an antiperspirant/ deodorantformula incorporating the quat salts and silicones according 35 to the present invention.

TABLE X Ingredient Weight % 40 Cyclopentasiloxane 39 Dimethicone 20 Aluminum Zirconium Trichlorohydrex Glycinate 15 Dihydroxypropyltrimonium Chloride 5.0 45 C18-C36 Acid Triglyceride 5.0 Microcrystalline Wax 3.0 Glycerin 8.0 50 Silica 2.5 Dimethicone Crosspolymer 1.0 Fragrance 0.5 Disodium EDTA 0.4 55 Butylated Hydroxytoluene 0.3 Citric Acid 0.3

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EXAMPLE 11

[0055] A toothpaste according to the present invention can be formulated with the ingredients listed under Table XI.

5 TABLE XI Ingredients Weight % Zeodent 115® 20.00 Glycerin 18.00 10 Xanthan Gum 7.00 Sodium Carboxymethyl Cellulose 0.50 Sodium Bicarbonate 2.50

15 Dihydroxypropyltrimonium Chloride 2.00 Sodium Laurylsulfate 1.50 Sodium Fluoride 1.10 Sodium Saccharin 0.40 20 Titanium Dioxide 1.00 Pluronic F-127® 2.00 FD&C Blue No. 1 3.30 25 Menthol 0.80 PEG-10 Dimethicone 0.50 Water balance

30 EXAMPLE 12

[0056] This Example details the synthesis of 2,3-dihydroxypropyl trimethylammonium chloride (identified in Table XII as dihydroxypropyl trimonium chloride). A 125 ml erlenmeyer flask was charged with 16.7 ml (53 mmol) of 3-chloro-2- hydroxypropyl trimethylammonium chloride (employed as a 60% material in water as Quat 188®). The flask was equipped 35 with a dropping funnel and stirring bar. A solution of sodium hydroxide (55 ml, 55.0 mmol) was charged into the flask via the dropping funnel at a rate to maintain room temperature of the reaction. Once addition was complete, the solution was stirred under ambient conditions for about 12 hours, followed by heating at 50°C for two hours. [0057] Progress of the reaction was monitored by thin layer chromatography (TLC). Product was spotted on a 2.5 by 7.6 cm silica gel plate alongside the starting material and eluted with butanol: acetic acid: water (4: 2:2) for approximately 40 50 minutes. Visualization was executed with ninhydrin stain and scorching on a hotplate. [0058] Crude product solution was first acidified to pH of 7, and then concentrated to remove water. Ethanol (200 ml) was added to the crude product with stirring. Upon sitting, sodium chloride precipitated and was filtered off under vacuum. The filtrate was concentrated under vacuum on a Rotavap®, followed by additional drying under high vacuum (0.05 mmHg). A cloudy gel was obtained yielding the final product in 97% yield. TLC analysis indicated a major spot at R = 0.27. 45 f [0059] A 60 MHz proton NMR (D2O w/TSP) was run on the final product. The spectra confirmed the final product structure. Mass Spectrum analysis in positive ion mode revealed a M+ of 134 (minus chlorine).

EXAMPLE 13

50 [0060] A series of experiments were conducted to evaluate skinfeel performance through instrumentation. A series of samples 1 through 5c were prepared for evaluation in a stick/ slip friction test. Base formula for all of the samples was a 20% aqueous glycerin solution thickened with 2% Carbopol 980® into which varying amounts of dihydroxypropyltrimonium chloride and dimethicone (DC 200/50) were blended.

55 Measurement of Stick or Tack

[0061] A measured amount of each sample (200 microliters) was applied to a one-inch diameter layer of closed cell

12 EP 1 804 922 B1

neoprene mounted on a stainless steel plate. The plate was mounted on the crosshead of an Instron Model 4.501 Universal Testing Instrument (Instron Corp., Canton, MA). Another one- inch diameter layer of closed cell neoprene was attached to a stainless steel plate, which was mounted to a compression load cell on the Instron’s Load Frame. The two layers were compressed at a rate of 10 cm/min to a compression force of 100 grams and then separated at a rate of 10 5 cm/min. The force of separation is defined as Stick or Tack and is measured in grams. Each sample was run five times.

Measurement of Sliding Friction

[0062] An excess amount of each sample was applied to a glass and drawn down to a film of 75 microns thick, 6 10 inches long and 0.5 inches wide using a drawdown knife. The plate was mounted on the crosshead of an Instron Model 4501 Universal Testing Instrument. An aluminum sled measuring 7.6 cm by 2.5 cm and weighing 19 grams was attached to the lnstron’s Load Cell. After allowing the film to dry for one minute the sled was pulled across the surface at 10 cm/min. The average amount of work is defined as Sliding Friction and is measured in gram-cm.

15 TABLE XII Sample No. Glycerol Quat (%) Dimethicone (%) Stick (Tack, g) Friction g-cm 1 0.0 0.0 67.0 2081 2 0.1 0.0 37.3 1394 20 3a 0.0 0.1 66.4 2243 3b 0.0 0.5 66.5 2396 3c 0.0 1.0 67.0 2756

25 4a 0.1 0.1 37.6 1783 4b 0.1 0.5 41.9 2016 4c 0.1 1.0 46.6 2341 4ai 0.2 0.2 35.6 1777 30 4bi 0.2 1.0 44.5 1966 4ci 0.2 2.0 46.4 2443 4aii 1.0 1.0 39.3 1953 35 4bii 1.0 5.0 45.1 2274 4cii 1.0 10.0 45.5 2563 5a 5.0 0.0 34.5 2189 5b 5.0 1.0 40.7 1470 40 5c 10.0 1.0 40.9 1272

[0063] Higher numbers for "tack" indicate greater stickiness of the sample. Higher "friction" values relate to increased dry. Thus, lower values for tack and friction indicate better aspects of skinfeel. 45 [0064] Samples 3a through 3c are formulated with dimethicone. These formulas all have relatively high stick and friction values. Samples 4a through 5c demonstrate that addition of dihydroxypropyltrimonium chloride (glycerol quat) has a significantly positive effect upon reducing tack and friction of the formulas.

50 Claims

1. A personal care composition comprising:

(i) from 0.05% to 30% by weight of a dihydroxypropyl quaternary ammonium salt of structure AB, wherein 55

A is a cationic charged component of the salt AB, B is an anionic charged component of the salt AB, and

13 EP 1 804 922 B1

A has a single quaternized nitrogen atom, at least two hydroxy groups and a molecular weight no higher than about 250;

(ii) from 0.05 to 50% by weight of a silicone. 5

2. The composition according to claim 1 wherein the quaternary ammonium salt is a dihydroxypropyltri(C1-C3 alkyl) ammonium salt.

3. The composition according to claim 2 wherein the salt is dihydroxypropyltrimonium chloride. 10 4. The composition according to any one of the preceding claims which is selected from the group consisting of leave- on skin lotions and creams, shampoos, hair conditioners, shower gels, toilette bars, antiperspirants, deodorants, dental products, shave creams, depilatories, lipsticks, foundations, mascara, sunless tanner and sunscreen lotions.

15 5. The composition according to any one of the preceding claims wherein the silicone is a cyclomethicone.

6. The composition according to any one of the preceding claims wherein the silicone is dimethicone.

7. The composition according to claims any one of the preceding claims 20 wherein the silicone is a dimethicone/vinyl dimethicone crosspolymer.

8. A method for moisturizing human body parts while still providing an aesthetically pleasing skinfeel comprising the step of topically applying to the human body parts a personal care composition comprising from 0.05 to 30% by weight of a quaternary ammonium salt which is a salt of structure AB 25 wherein

A is a cationic charged component of the salt AB, B is an anionic charged component of the salt AB, and A has a single quaternized nitrogen atom, at least two hydroxy groups and a molecular weight no higher than 30 250; and from 0.05 to 0% of silicone by weight of the composition.

Patentansprüche

35 1. Körperpflegezusammensetzung, umfassend:

(i) 0,05 % bis 30 Gewichtsprozent eines quaternären Dihydroxypropylammoniumsalzes der Struktur AB, worin

40 A eine kationisch geladene Komponente des Salzes AB darstellt, B eine anionisch geladene Komponente des Salzes AB darstellt, und A ein einzelnes quaternisiertes Stickstoffatom, mindestens zwei Hydroxygruppen und ein Molekulargewicht nicht höher als etwa 250 aufweist;

45 (ii) 0,05 bis 50 Gewichtsprozent von einem Silikon.

2. Zusammensetzung nach Anspruch 1, worin das quaternäre Ammoniumsalz ein Dihydroxypropyltri (C1-C3-alkyl) ammoniumsalz ist.

50 3. Zusammensetzung nach Anspruch 2, worin das Salz Dihydroxypropyltrimoniumchlorid darstellt.

4. Zusammensetzung nach einem der vorangehenden Ansprüche, die aus der Gruppe, bestehend aus Leave-on- Hautlotionen und -Cremes, Shampoos, Haarkonditionierern, Duschgelen, Toilettenriegeln, schweißhemmenden Mitteln, Deodorantien, Dentalprodukten, Rasiercremes, Enthaarungsmitteln, Lippenstiften, Grundierungen, Masca- 55 ra, sonnenlosen Bräunungsmitteln und Sonnenschutzlotionen, ausgewählt ist.

5. Zusammensetzung nach einem der vorangehenden Ansprüche, worin das Silikon ein Cyclomethicon darstellt.

14 EP 1 804 922 B1

6. Zusammensetzung nach einem der vorangehenden Ansprüche, worin das Silikon Dimethicon darstellt.

7. Zusammensetzung nach einem der vorangehenden Ansprüche, 5 worin das Silikon ein Dimethicon / Vinyldimethicon-Crosspolymer darstellt.

8. Verfahren zum Befeuchten menschlicher Körperteile, während noch ein ästhetisch angenehmes Hautgefühl bereit- gestellt wird, umfassend den Schritt des örtlichen Auftragens auf die menschlichen Körperteile einer Körperpflege- zusammensetzung, umfassend 0,05 bis 30 Gewichtsprozent eines quaternären Ammoniumsalzes, wobei das Salz 10 die Struktur AB aufweist, worin

A eine kationisch geladene Komponente des Salzes AB darstellt, B eine anionisch geladene Komponente des Salzes AB darstellt, und 15 A ein einzelnes quaternisiertes Stickstoffatom, mindestens zwei Hydroxygruppen und ein Molekulargewicht nicht höher als etwa 250 aufweist; und

von 0,05 bis 0 Gewichtsprozent der Zusammensetzung Silikon.

20 Revendications

1. Composition de produit d’hygiène personnelle comprenant .

25 (i) de 0,05 % à 30 % en poids d’un sel de dihydroxypropyl-ammonium quaternaire de structure AB, où

A est un composant chargé cationique du sel AB, B est un composant chargé anionique du sel AB, et 30 A a un seul atome d’azote quaternisé, au moins deux groupes hydroxy et un poids moléculaire qui n’est pas supérieur à 250 ;

(ii) de 0,05 à environ 50 % en poids d’un composé siliconé.

35 2. Composition selon la revendication 1, dans laquelle le sel d’ammonium quaternaire est un sel de dihydroxypropyltri(alkyl en C1 à C3) ammonium.

3. Composition selon la revendication 2, dans laquelle le sel est le chlorure de dihydroxypropyl-trimonium.

40 4. Composition selon l’une quelconque des revendications précédentes qui est choisie dans le groupe constitué de lotions et de crèmes à ne pas rincer, de shampooings, d’après-shampooings, de gels de douche, de pains de toilette, d’antiperspirants, de déodorants, de produits dentaires, de crèmes à raser, de dépilatoires, de rouges à lèvres, de fonds de teint, de mascara, de lotions auto-bronzantes et écrans solaires.

45 5. Composition selon l’une quelconque des revendications précédentes, dans laquelle le composé siliconé est un cyclométhicone.

6. Composition selon l’une quelconque des revendications précédentes, dans laquelle le composé siliconé est le diméthicone. 50 7. Composition selon l’une quelconque des revendications précédentes, dans laquelle le composé siliconé est un polymère réticulé de diméthicone/vinyl-diméthicone.

8. Méthode d’hydratation de parties du corps humain tout en fournissant tout de même une texture plaisante d’un point 55 de vue esthétique comprenant l’étape d’application topique sur les parties du corps humain d’une composition de produit d’hygiène personnelle comprenant de 0,05 % à 30 % en poids d’un sel d’ammonium quaternaire de structure AB, où

15 EP 1 804 922 B1

A est un composant chargé cationique du sel AB, B est un composant chargé anionique du sel AB, et A a un seul atome d’azote quaternisé, au moins deux groupes hydroxy et un poids moléculaire qui n’est pas supérieur à 250 ; et 5 de 0,05 à 0 % d’un composé siliconé en poids de la composition.

16 EP 1 804 922 B1

REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• US 6869977 B1 [0005]